Interview with Andrew Ray, CEO of Taxwire

Introduction

• Andrew Ray, co-founder and CEO of Taxwire, joins the show.
• Discusses initial connection during early COVID years on Twitter.
• Reflection on how COVID offered a unique time for online networking.

Background and Career Path

Early Career

• Grew up in a small town in Ohio; humble beginnings.
• Parents were hardworking, but lacked higher education.
• Worked multiple jobs to fund college.

Breaking into Tech

• Initially aimed for Wall Street.
• Became interested in tech after reading about venture capital.
• Started a small business in the Midwest; not successful but sold without losing money.
• Worked at a venture fund in the Midwest.

Transition to the Coasts

• Recognized limitations of being in a tertiary tech ecosystem.
• Used Twitter to build a network.
• Joined On Deck after DMing Eric Torenberg, leading to significant career growth.

Current Role: Taxwire

Overview of Taxwire

• Taxwire helps software companies with sales tax compliance.
• Focus on B2B SaaS, AI, ecommerce brands, and accounting firms.

The Problem Solved

• Companies face complex sales tax issues when expanding rapidly across states/countries.
• Taxwire simplifies initial compliance, registration, tax filing, and integration.

Founding Story

• Came from personal experience with sales tax issues at a previous company.
• Initial reluctance to start a company in the "boring" tax space.
• Ultimately saw the business opportunity after advice from friends and co-founders.

Fundraising and Building a Company

Experience in Fundraising

• Importance of building a network and reputation prior to fundraising.
• Leveraged connections made at On Deck and Party Round for introductions.
• Raised funds with a blend of strategic introductions and leveraging past relationships.

Challenges and Insights

• Emphasized the difficulty of fundraising without social capital.
• Need for warm introductions and credibility.
• Strategic approach to fundraising through learned experience and networking.

Navigating the Tech Industry

Insight into Tech Hubs

• Acknowledges the challenges of building a tech company outside major hubs like SF or NYC.
• Discusses options and strategies for founders in non-hub locations.

Advice for Outsiders

• Emphasizes building better "cards" or social capital to succeed.
• Recognizes the importance of being part of a network and the role of accelerators like YC.

Closing Thoughts

• Andrew encourages networking and hard work as key to breaking into tech.
• Highlighted the importance of persistence and strategic positioning in the industry.

Contact Information

• Andrew can be reached on Twitter, LinkedIn, and Substack.
• Encourages reaching out for advice or collaboration.